Tert-Butyl isocyanide → HCID 74762783, compound

Participants

Reaction Steps

5-(trifluoromethyl)pyridin-2-amine (0.5 g, 3.08 mmol, Eq: 1.00), 3-bromobenzaldehyde (599 mg, 378 μL, 3.24 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (176 mg, 925 μmol, Eq: 0.3) were dissolved in MeOH (4 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (256 mg, 351 μL, 3.08 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 14 h. The solvent was removed and the crude product was purified by flash column chromatography (hexane/AcOEt 100/0 to 0/100) to yield a light yellow solid (865 mg, 68.0%). MS: 414.0 [M+H]+; 1H-NMR (D6-DMSO): δ 8.90 (s, 1H), 8.48 (s, 1H), 8.26 (d, 1H), 7.72 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 7.40 (t, 1H), 4.96 (s, 1H), 1.05 (s, 9H).

Provenance & Evidence